Travel Guide: 5 days in Maui, Hawaii

Travel Guide: 5 days in Maui, Hawaii

Is it a coincidence that Southwest Airlines released flights to Hawaii on March 4, 2019, and this post comes just 8 months after? My family and I had been waiting for flights to Hawaii since Southwest began the process of becoming verified to fly there back in early 2018, so the second they released flights (they never announced a date, it was a surprise to everyone) we immediately starting researching flight options. Flights were literally flying off the shelves and we knew we had to act fast for the Wanna Get Away fare. We knew flights would be most affordable out of California (more on that here), so we started searching for flights out of Los Angeles and Oakland. My parents and I both have companion pass, so all we needed were 2 tickets for my sister, parents, and I. 10 minutes and 14,000 points (!!!!) later, we had roundtrip flights from Oakland to Maui. We later booked Dallas to Oakland roundtrip Southwest flights for $150.

ANYWAYS, that’s the story of how I got there (which I always love sharing) and now here’s everything we did in our 5 dreamy days on the island of Maui.

Where to stay in Maui

Maui is a small island and you can pretty much see every part of it in your entire stay. With the nearly 6-hour plane ride (even longer if you’re traveling from somewhere other than California), I highly suggest staying at least 5 days to ensure you get to see everything.

Maui is divided into 4 shores – North (Paia, Wailuku), East (Hana), South (Wailea), and West (Lahaina and Kaanapali). We stayed at the Marriott Vacation Club in Kaanapali, which is a nice resort town right on the beach with a golf course, a multitude of hotels, and plenty of things to do within walking distance. The whole beach of Kaanapali is lined with resorts, public access to the beach, hundreds of lawn chairs and hammocks, and an outdoor shopping area with boutiques, coffee shops, an awesome restaurant called MonkeyPod, and smoothie cafes.

The Marriott exceeded our expectations and had lawn yoga every morning, a Starbucks on the beach, 2 pools, free poolside snacks every day from popcorn to snow cones, and a poolside bar. We spent 2 days just hanging around the hotel pool and relaxing in the hundreds of hammocks.

What to do in Maui

From water activities, excursions, and luaus, I’ve listed a few must-dos in Maui.

RELAX! & Eat Fresh, Healthy Food

The best part about vacationing in Maui is you don’t have to do anything at all! The sun is hot, the waves are crashing, and the food is fresh. After a hectic summer of European travel and a wedding in Cancun, we were ready to relax, enjoy the sun, and eat allllll the acai and poke bowls. There was an amazing coffee shop in Kaanapali’s outdoor shopping center, Whalers Village, called Island Vintage. We walked here early for coffee and acai bowls and enjoyed sitting outside and people watching! I loved the Hawaiian Honey Latte, Island Latte, Moana Bowl, and the Lox of Bagel.

Another place we found delicious fresh food at was the Maui Farmers Market. The outdoor market is only on certain days, but the indoor market is open every day. We ordered acai bowls, the best mango salsa I’ve ever had, homemade chips, and fresh guacamole. We walked across the street to the beach, found a spot in the shade, and enjoyed our snacks!


Visit the World’s Best Beaches & Book a Snorkeling Excursion

Maui is home to some of the best beaches and snorkeling in the WORLD. The water is crystal clear and warm and the coral is unreal. The prettiest beaches we visited were:

  • Black Rock Beach (west shore)
    • Rent snorkeling gear and swim along the black rocks to see turtles, coral, and millions of fish
  • Napili Beach (west shore)
  • Maluaka (south shore)
    • Venture over here early in your day and stop by Kihea Cafe for the best coconut pancakes you’ll ever have!

You can’t visit Maui without taking at least one guided snorkeling trip. There are plenty of excursion kiosks in Kaanapali (or wherever you’re staying), so just pick one and start inquiring about snorkeling tours. We booked the Gemini Charter because it had the best reviews for crew, route, open bar, and lunch!

We were on the boat for a total of 4 hours and stopped in Honolua Bay to snorkel. We saw so many turtles and they even had a photographer documenting everything for us in the water! I would recommend this snorkeling tour to everyone, it was truly a highlight of the trip.

Watch the Sunset on an Evening Boat Ride

The sunset in Maui is truly one of the most amazing sunsets I’ve ever seen! We had a perfect view of it from the beach in front of our hotel but we knew it would be even more lovely from the water. Recommended by a friend, we booked the Sea Maui Sunset Live boat tour. It was an awesome experience and my whole family loved it! We chose the “Live” tour because it included live music, snacks, and an open bar. The live music was honestly one of the best parts. Our group danced all through sunset and even went out together afterwards!


Visit North Shore for Shopping, Sea Turtle Watching, & Mamas Fish House

Baldwin Avenue Shopping & Sipping

One of our most memorable days was the day we spent in North shore. When planning travel itineraries, I like to do all my research to locate where everything is so I can make our dining reservations in the same vicinity as our daytime activities. Paia, the quaint little town in North shore, is home to the best surf waves, Baldwin Avenue, and the popular Ho’okipa Beach Park where the sea turtles migrate after their long day. We arrived in Paia around 3 pm, shopped on Baldwin Avenue, and enjoyed happy hour at one of the little cafes. I really wanted to try Paia Bay Coffee & Bar but to my luck, their power was out. If you’re in Paia, you must go for me!


Ho’okipa Beach Park for Sunset & Turtle Watching

After happy hour, we headed to the beach park to watch the sunset and the sea turtles migrate to shore. I have no words for how many sea turtles we saw! From afar, they look like large rocks! You’re allowed to walk down the beach and up to the rope, but the turtles are protected and you can’t get too close. If you’re in Maui, you have to see the turtles at least once. I have a whole new respect for the amazing animal!

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Dine at the Famous Mama’s Fish House

Everyone’s talking about it so you know you have to go. Mama’s Fish House is more than a restaurant, it’s an experience! It sits right on the beach – you literally walk through the sand to get to the door. This restaurant was a must when planning our vacation so I made a reservation 5 weeks in advance! We ordered:

  • Haleakala Ranch Beef – it comes in a grilled papaya, hello Hawaii!
  • Autumn Salad
  • Braised Short Ribs
  • Select fish of the day (it changes every day!)
  • Coconut Chiffon Cake (So creamy and moist!)
  • Creme Brulee (just order it)
  • Strawberry Guava Fizz Cocktail
  • Pink Hibiscus Cocktail

Enjoy Lahaina for Happy Hour, Sunset, & Nightlife

Lahaina is the town just 10 minutes south of Kaanapali right along the coast. The town is lively and has so many restaurants and bars lining Front Street. We came here for 2 nights because it’s definitely where the fun is at night!

Fleetwoods for Happy Hour or Dinner

Our favorite meal of the vacation was actually at Fleetwoods! This is Mick Fleetwood’s 2-story bar and restaurant and it is such a good time! The rooftop has an amazing sunset view, live music, and great bar. Downstairs you’ll find a whole shop dedicated to merch and Mick. We enjoyed happy hour on the rooftop, although we couldn’t find a seat so we had to stand. We loved the vibe so much that we made a dinner reservation for the next night! I made to sure to include that we wanted to be seated outside which wasn’t a problem at all. Everything from the atmosphere, drinks (get the Kokomo, I’m still thinking about it), the food (try the gnocchi and mac n cheese!), and view was spectacular.


Other Honorable Mention Restaurants on Front Street

  • Lahaina Fish Co – We ate here one night and it was good but not amazing
  • Lahaina Grill
  • Lahaina Pizza
  • Down the Hatch – The best nightlife in Lahaina! The restaurant and bar is outside and decorated so cute! We arrived at around 9 pm after our sunset cruise and we were able to find a table to order drinks and food. The chicken sandwich was to die for! It started filling up around 10:30 and a band came out! The vibes were awesome and everyone was super nice. It’s definitely a local spot for young people.

More Must-Do’s in Maui

The last time I visited Hawaii was in 2001. We did a lot of the classic things them but if this is your first time you must do the following:

Experience a Luau

Of course when you’re in Hawaii, you need to attend a Luau! I really wanted to do one on this trip but the nicer ones were either booked or didn’t fit with our schedules. If you’re wanting a specific night or luau, visit any of the kiosks or hotel concierge at the beginning of your trip to reserve your spot. There’s tons of options so just be sure to ask which ones are the most popular!

Embark on The Road to Hana

Everyone asked me if we did this and honestly, no we didn’t! The Road to Hana is extremely popular for tourists for obvious reasons. The Road to Hana is basically a road trip from Paia in North shore all the way to the east side of the island to Hana. The journey is filled with jungle, waterfalls, hikes, forests, and amazing views. However, it takes awhile and it is suggested you begin as early as 6 am because of the narrow roads. We opted out because we were only there for 5 days and didn’t want to spend a whole day in the car. My family and I were on the fence about the Road to Hana for basically our entire trip, and then we eventually decided to nix it. If we had a few more days I know we definitely would’ve done it!

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Maui was truly a dream and I can’t wait to visit again! The food, people, sunsets, and beaches make this a truly one-of-a-kind vacation. And you don’t even need a passport!

That’s all for now, friends!

Happy traveling,




  1. February 15, 2020 / 11:47 pm

    Great content! Super high-quality! Keep it up! 🙂

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